15 MLB Players Who Let a Contract Go Straight to Their Heads

Big contracts can change a player’s life—but sometimes, they change a little too much. Whether it was a dip in performance, a sudden attitude shift, or a newfound obsession with their “brand,” these guys let the money talk a little louder than their bats.

These aren’t just overpaid players—they’re stars who acted like they’d already punched their Hall of Fame ticket the moment the ink dried. From clubhouse divas to disappearing acts, these 15 players reminded us that money might buy a mansion, but it doesn’t always buy humility.

15. Jason Heyward

San Diego Padres left fielder Jason Heyward (22) celebrates after hitting a double during the fourth inning against the San Francisco Giants at Petco Park.
Denis Poroy / Imagn Images

Heyward cashed in big after a strong season and a strong reputation—but never quite lived up to the hype. His bat went quiet while his paycheck kept screaming.

14. Yoenis Céspedes

Jul 24, 2020; New York City, New York, USA; New York Mets outfielder Yoenis Cespedes (52) follows through on a solo home run against the Atlanta Braves during the seventh inning of an opening day game at Citi Field. Mandatory Credit: Brad Penner-Imagn Images
Brad Penner-Imagn Images

Once the Mets backed up the Brinks truck, Céspedes seemingly started prioritizing everything but baseball. Golf injuries, wild disappearances—his contract years felt more like a reality show.

13. Josh Hamilton

File The Reds struck gold when they acquired Josh Hamilton from the Cubs on the day of the 2006 Rule 5 Draft. This year's version takes place Thursday. The Reds struck gold when they acquired Josh Hamilton from the Cubs on the day of the 2006 Rule 5 Draft. This year's version takes place Thursday. Cincinnati Reds Opening Day 2007 Reds Vs Cubs At Great American Ball Park
Ernest Coleman, Cincinnati Enquirer via Imagn Content Services, LLC

Hamilton’s story was already dramatic, and the massive deal with the Angels added another wild chapter. Expectations were sky-high, but his production plummeted just as fast as his discipline.

12. Jacoby Ellsbury

Feb 20, 2018; Tampa, FL, USA; New York Yankees center fielder Jacoby Ellsbury (22) works out during spring training at George M. Steinbrenner Field. Mandatory Credit: Kim Klement-Imagn Images
Kim Klement-Imagn Images

The Yankees paid big, and Ellsbury basically vanished into thin air. For years, fans wondered if he was still on the roster—or on a beach somewhere spending his millions.

11. B.J. Upton

Atlanta Braves center fielder B.J. Upton (2) catches a ball for an out against Washington Nationals second baseman Asdrubal Cabrera (not pictured) in the third inning at Turner Field.
Jason Getz / Imagn Images

After signing a big deal with the Braves, Upton transformed from a solid outfielder into one of the league’s biggest mysteries. The swagger stayed, but the swing didn’t.

10. Barry Zito

San Francisco Giants pitcher Barry Zito pitches against the Milwaukee Brewers during the spring game at Scottsdale Stadium March 4, 2010. Sr Giants0306 163374
David Wallace / The Arizona Republic, Arizona Republic via Imagn Content Services, LLC

Zito went from Cy Young winner to San Francisco’s most expensive enigma. His contract felt like an anchor, dragging his performance down for years.

9. Pablo Sandoval

Mar 26, 2024; San Francisco, California, USA; San Francisco Giants third baseman Pablo Sandoval smiles as he is removed for a pinch runner after singling against the Oakland Athletics during the ninth inning at Oracle Park. Mandatory Credit: D. Ross Cameron-Imagn Images
D. Ross Cameron-Imagn Images

The “Kung Fu Panda” got a fat contract—and then, well, just got fat. His time in Boston was more about waistlines than win totals.

8. Carl Crawford

May 6, 2016; Toronto, Ontario, CAN; Los Angeles Dodgers left fielder Carl Crawford (3) reacts after hitting a single during the third inning in a game against the Toronto Blue Jays at Rogers Centre. The Toronto Blue Jays won 5-2. Mandatory Credit: Nick Turchiaro-Imagn Images
Nick Turchiaro-Imagn Images

Crawford was a speedster who got a megadeal and promptly lost his spark. Injuries and inconsistency turned that contract into a cautionary tale.

7. Chris Davis

Jul 9, 2020; Baltimore, Maryland, United States; Baltimore Orioles first baseman Chris Davis (19) returns to the dugout during a practice game at Oriole Park at Camden Yards. Mandatory Credit: Mitch Stringer-Imagn Images
Mitch Stringer-Imagn Images

Davis hit bombs, got paid, and then forgot how to hit altogether. His contract became the punchline of every Orioles conversation for years.

6. Miguel Cabrera

Detroit Tigers designated hitter Miguel Cabrera makes his last play at first base as a Tiger during eighth inning action on Sunday, Oct. 1, 2023.
Kirthmon F. Dozier / USA TODAY NETWORK

Yes, Miggy is an all-time great—but after he got the mega-extension, the production dipped while the paycheck stayed elite. He earned his money early, but the later years were rough.

5. Alex Rodriguez

Former New York Yankees third baseman Alex Rodriguez at Yankee Stadium.
Wendell Cruz / Imagn Images

A-Rod always had talent, but once he got those monster deals, the ego ballooned. From scandals to suspensions, it felt like the money only fueled the drama.

4. Albert Pujols

Los Angeles Dodgers pinch hitter Albert Pujols hits against the St. Louis Cardinals during the ninth inning of the National League Wild Card Game at Dodger Stadium on Oct 6, 2021.
Robert Hanashiro / USA TODAY NETWORK via Imagn Images

Pujols was a legend in St. Louis, but after his massive Angels contract, he never quite looked the same. The numbers dipped, the legs slowed, and the contract loomed large.

3. Matt Kemp

Sep 15, 2020; Denver, Colorado, USA; Colorado Rockies designated hitter Matt Kemp (25) tosses his bat after striking out in the eighth inning against the Oakland Athletics at Coors Field. Mandatory Credit: Isaiah J. Downing-Imagn Images
Isaiah J. Downing-Imagn Images

Kemp got paid like a superstar and started acting like one—even when his performance didn’t back it up. Injuries and inconsistency followed him around after the payday.

Read More: Ranking the 30 Most Overpaid Quarterbacks of All Time

2. Prince Fielder

Jun 19, 2025; Birmingham, AL, USA; West team first baseman Prince Fielder (28) jogs to first base during the East-West Classic at Rickwood Field. Mandatory Credit: David Leong-Imagn Images
David Leong-Imagn Images

Fielder signed a huge deal and brought big expectations, but his bat never quite matched the billing. Health issues cut his career short, but that contract still felt like a swing and a miss.

Read More: The 15 Worst Free-Agent Contracts in MLB History

1. Bryce Harper

May 23, 2025; West Sacramento, California, USA; Philadelphia Phillies first baseman Bryce Harper (3) is looked at by a trainer after being hit by a pitch against the Athletics during the sixth inning at Sutter Health Park. Mandatory Credit: Dennis Lee-Imagn Images
Dennis Lee-Imagn Images

Harper leaned into the superstar image the moment he got paid, embracing the spotlight like it was part of the deal. He’s delivered big moments—but the ego definitely showed up just as loud as the bat.

Read More: 20 MLB Stars Who Got Exposed When They Switched Teams

Related Articles
Pete Rose
The 17 Most Pesky MLB Stars of All Time
Whether it was their relentless hustle or pesky plate approach, these 17 MLB stars made their careers...
Read More
Retired Pittsburgh Steelershead coach Bill Cowher is recognized at halftime of the Seattle Seahawks game for his induction into the Hall of Fame at Heinz Field.
The 13 Most Overrated NFL Coaches of All Time
From media darlings to guys who got too much credit for stacked rosters, we round up NFL coaches who’ve...
Read More
Jan 3, 2021; Philadelphia, Pennsylvania, USA; Philadelphia Eagles quarterback Jalen Hurts (2) celebrates with teammates after a touchdown run against the Washington Football Team during the second quarter at Lincoln Financial Field. Mandatory Credit: Bill Streicher-Imagn Images
15 NFL Teams Everyone Secretly Loved to See Fail
For one reason or another, when these squads crash and burn, football fans everywhere can’t help but...
Read More
Carson Wentz
14 NFL Receivers With Hands Like Bricks
These NFL receivers were known for drops that made fans groan. Discover 14 wideouts with hands like bricks...
Read More
Dec 20, 2009; Dallas, TX, USA; Cleveland Cavaliers center Shaquille O'Neal (33) shoots a free throw against the Dallas Mavericks at American Airlines Arena. Mandatory Credit: Photo By Matthew Emmons-USA TODAY Sports
13 NBA Big Men Who Couldn’t Hit Free Throws
Whether it was nerves, mechanics, or just plain bad luck, these NBA big men turned every trip to the...
Read More
Dec 20, 2009; Denver, CO, USA; Oakland Raiders quarterback JaMarcus Russell (2) walks off the field after the Raiders' 20-19 victory over the Denver Broncos at Invesco Field. Mandatory Credit: Kirby Lee/Image of Sport-Imagn Images
12 Quarterbacks Who Had No Pocket Awareness
These 12 quarterbacks had all the tools—except pocket awareness. See who froze under pressure and made...
Read More

As an Amazon Associate, The Quick Report earns from qualifying purchases.

Part of the Castaway Studios media network.